However, he found opportunities in the starting XI limited, as coach José Mourinho stated: He scored in his first Serie A match against Catania Calcio, with one of his trademark trivelas in a 2–1 home win. On 1 September 2008, Quaresma signed for Italian champions Inter Milan in a cash/player exchange fee of €18.6 million, with youngster Pelé joining Porto. In the penalty shootout defeat of Once Caldas in the Intercontinental Cup, he successfully converted his attempt in an 8–7 victory in Yokohama. Quaresma scored five goals in his first year at the Estádio do Dragão, and the club finished as runners-up. Benfica in the Supertaça Cândido de Oliveira, and also scored in the 2–1 loss to Valencia CF in the UEFA Super Cup.

He started the campaign on a high note by scoring the only goal in a win against S.L. Quaresma signed for FC Porto in the summer of 2004 as Deco moved in the opposite direction for a fee of €15 million plus Quaresma, valued at €6 million. Shortly after, he announced his refusal to play for the Spanish club as long as manager Frank Rijkaard was in charge. Quaresma injured his right foot in the final weeks of the season, forcing him to miss both the 2004 UEFA European Under-21 Championship and UEFA Euro 2004 tournaments.

In his first year in La Liga he made ten starts and 12 substitute appearances, scoring in the 5–0 home rout of Albacete Balompié. In 2003, Quaresma was sold to FC Barcelona for a reported €6 million fee and the loan of Fábio Rochemback. Under the same coach, Quaresma scored five times in the league the following campaign, but the team could only finish in third place. A trainee at Sporting CP's famed academy, the 17-year-old was promoted to the first team by manager László Bölöni before the start of the 2001–02 season, playing 28 Primeira Liga matches and scoring three goals as the team won the double.

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